Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B69/00—Dyes not provided for by a single group of this subclass
  • C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
  • C09B69/06—Dyestuff salts, e.g. salts of acid dyes with basic dyes of cationic dyes with organic acids or with inorganic complex acids
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0001—Post-treatment of organic pigments or dyes
  • C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0001—Post-treatment of organic pigments or dyes
  • C09B67/0017—Influencing the physical properties by treatment with an acid, H2SO4
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0001—Post-treatment of organic pigments or dyes
  • C09B67/002—Influencing the physical properties by treatment with an amine

Definitions

• the pigments prepared by the prior art processes give hard agglomerates and aggregates when the aqueous press cake is dried, and it is therefore difficult to convert these dried pigments to offset printing inks which are readily dispersible and possess a small particle size.
• nitrocellulose-containing printing inks which contain these pigments frequently exhibit insufficient gloss and poor transparency on acetate film and aluminum foil.
• sulfuric acid half esters based on C 10 -C 20 -fatty alcohols, fatty alcohol/ethylene oxide adducts or C 5 -C 20 -alkylphenol/ethylene oxide adducts,
• naphthols or C 1 -C 20 -alkylphenols, or mixtures of these agents are added to the aqueous mixture before, during or after the laking procedure, and the crude pigment in the aqueous suspension is heated to 50°-100° C. at pH 2-5.
• the pigment is then isolated, washed and dried.
• the central feature of the process according to the invention is the fact that the lake obtained in the conversion, also referred to below as the crude pigment, is heated, in the form of an aqueous suspension, to 50°-100° C. in the presence of the agents (1) to (9) used according to the invention, or a mixture of these, at a pH of from 2 to 5.
• Suitable additives for the process are:
• additives are:
• Alkylaminoalkanoic acids preferably N-C 8 -C 18 -alkylaminobutyric acids, such as N-C 18 -alkylaminobutyric acid, N-C 16 -alkylaminobutyric acid, N-coconut fat- ⁇ -aminobutyric acid, N-C 14 -alkylaminobutyric acid, N-C 12 -alkylaminobutyric acid, N-C 10 -alkylaminobutyric acid and N-C 8 -alkylaminobutyric acid.
• N-C 8 -C 18 -alkylaminobutyric acids such as N-C 18 -alkylaminobutyric acid, N-C 16 -alkylaminobutyric acid, N-coconut fat- ⁇ -aminobutyric acid, N-C 14 -alkylaminobutyric acid, N-C 12 -alkylaminobutyric acid, N-C
• Diaryl- and triarylamines diphenylamine, N-methyldiphenylamine, N-ethyldiphenylamine, N-4-methylphenylaniline, N-4-methoxyphenylaniline, triphenylamine, N-phenyl-naphthylamine.
• Neutral phosphates tri-C 3 -C 18 -alkyl phosphates, such as tri-n-propyl phosphate, tributyl phosphate, trihexyl phosphate, trioctyl phosphate, trinonyl phosphate, tridecyl phosphate, tridodecyl phosphate, tritetradecyl phosphate, trihexadecyl phosphate and trioctyldecyl phosphate, these esters preferably being used together with nonionic assistants (7).
• tri-C 3 -C 18 -alkyl phosphates such as tri-n-propyl phosphate, tributyl phosphate, trihexyl phosphate, trioctyl phosphate, trinonyl phosphate, tridecyl phosphate, tridodecyl phosphate, tritetradecyl phosphate, trihexadecyl
• Acidic phosphates based on oxoalcohol fatty alcohol oxyalkylates such as fatty alcohol/EO and fatty alcohol/PO/EO adducts, polypropylene glycol, polyethylene glycol, and PO/EO block copolymers: mono- and diesters of phosphoric acid with reaction products of C 8 -C 20 -alkanols with EO, PO or PO+EO, such as C 8 -C 12 -oxoalcohols (mixtures) with from 2 to 50, preferably from 2 to 20, moles of EO per mole of alcohol, dodecanol with from 3 to 5 moles of EO, n- and isodecanol with from 3 to 5 moles of EO, C 12 -C 16 -alkanol mixtures with from 3 to 20 moles of EO, C 16 -alkanols with from 3 to 20 moles of EO, stearyl alcohol with from 3 to 20 moles of EO, my
• the acidic phosphates contain 1 or 2 of these radicals and are, as a rule, mixtures of the monoesters and diesters.
• Alkane- and alkenesulfonic acids, alkylbenzenesulfonic acids and alkylnaphthalenesulfonic acids n- and isooctanesulfonic acid, nonanesulfonic acid, decanesulfonic acid or dodecanesulfonic acid, tridecanesulfonic acid, tetradecanesulfonic acid, hexadecanesulfonic acid and octadecanesulfonic acid; hexylbenzenesulfonic acid, octylbenzenesulfonic acid, nonylbenzenesulfonic acid, decylbenzenesulfonic acid, dodecylbenzenesulfonic acid, tridecylbenzenesulfonic acid, tetradecylbenzenesulfonic acid, hexadecylbenzenesulfonic acid and octade
• Adducts of EO with alkylphenols, fatty alcohols and alkylamines Adducts of EO with alkylphenols, fatty alcohols and alkylamines:
• phenols are hexylphenol, isooctylphenol, nonylphenol, decylphenol, dodecylphenol, tridecylphenol, tetradecylphenol, hexadecylphenol and octadecylphenol with from 5 to 60, preferably from 5 to 30, moles of EO per mole of phenol;
• examples of suitable fatty alcohols are octanol, nonanol, decanol, dodecanol, tetradecanol, tridencanol, hexadecanol, octadecanol, C 8 -C 11 -oxoalcohol mixtures, C 11 -C 15 -oxoalcohol mixtures, a C 13 -C 15 -oxoalcohol mixture, coconut fatty alcohol, stearyl alcohol and palmityl alcohol with from 5 to 60, preferably from 5 to 25, moles of EO per mole of alcohol.
• alkanediols and alkanepolyols are glycol, propylene glycol, butane-1,4-diol, butane-1,2-diol, butane-2,3-diot, hexane-1,6-diol, octanediol, glycerol, butanetriol, trimethylolpropane and sorbitol.
• the EO content can be from 20 to 70% by weight, based on the polymer, the molecular weight can be from about 1000 to 50,000.
• Naphthols and alkylphenols ⁇ - and ⁇ -naphthol, 3,4-dimethylphenol, hexylphenol, octylphenol, nonylphenol and dodecylphenol.
• N-C 10 -C 20 -alkylamino-C 2 -C 8 -alkanoic acids in particular the N-C 10 -C 20 -alkylaminobutyric acids;
• the amounts of additives (1) to (11) are from 5 to 50, preferably from 10 to 45, % by weight, based on the amount of basic dye used for the laking procedure.
• the additives can be added before the laking procedure, for example to the solution of the basic dye or to the solution of the heteropolyacid, separately from the heteropolyacid during the laking procedure, or to the suspension of the lake after the laking procedure.
• the additives are used in the form of an aqueous solution or suspension.
• the after-treatment of the crude pigment (lake) is carried out at a pH of from 2 to 5, preferably from 2.2 to 4, and at from 50° to 100° C., preferably from 75° to 95° C., as a rule for from 10 to 120 minutes, preferably from 30 to 60 minutes.
• the amount of additive, the duration of the aftertreatment and the temperature at which it is carried out are dependent on the lakes.
• the optimum amounts of additive and the most advantageous temperature can be determined by simple series of experiments.
• a phosphomolybdic acid solution prepared in a conventional manner from 27.0 parts of molybdenum oxide and 2.55 parts of disodium phosphate in 255 parts of water was added to an aqueous solution of 38.6 parts of C.I. Basic Blue 7 (C.I. No. 42,595) in 2700 parts of water, the pigment being precipitated as a result of the addition.
• 4.9 parts of an acidic phosphate which contained, as the ester group, a product obtained by reacting a C 13 -C 15 -oxoalcohol mixture with 6 moles of PO and then with 12 moles of EO per mole of alcohol were added to this suspension.
• the pigment suspension was stirred for one hour at 75° C., after which 1.74 parts of sodium ethylenediaminetetraacetate and 8.3 parts of an emulsion prepared from 0.53 part of oleic acid ethanolamide, 1.13 parts of normal C 13 -C 15 -paraffin and 6.64 parts of water at 60° C. were added, as described in German Laid-Open Application DOS 2,707,972.
• the suspension was stirred for a further hour, after which the pigment was isolated, and dried in a through-circulation oven at 75° C. Milling gave a readily dispersible pigment which, when incorporated in an offset varnish, provided a printing ink having more finely divided particles and greater flow than that obtained using the pigment prepared as described in Comparative Example 1.
• Example 1 was repeated, except that, instead of the acidic phosphate stated there, a mixture of 3.9 parts of triisobutyl phosphate, 1.25 parts of an adduct of 20 moles of EO with 1 mole of isononylphenol and 0.29 part of an adduct of 5 moles of EO with 1 mole of isodecanol was used.
• the resulting pigment had virtually the same properties as the pigment prepared as described in Example 1.
• Example 2 The procedure described in Example 2 was followed, except that the laking procedure was carried out using a heteropolyacid solution prepared in a conventional manner from 80.7 parts of molybdenum oxide, 186.5 parts of tungsten oxide and 27.6 parts of disodium phosphate in 1200 parts of water.
• the pigment obtained Compared with the product obtained as described in German Laid-Open Application DOS 2,707,972, Example 3, the pigment obtained had the advantageous performance characteristics stated in Example 1, when used in offset inks and nitrocellulose-containing inks.
• Example 2 The procedure described in Example 1 was repeated, except that, instead of C.I. Basic Blue 7, 35.9 parts of C.I. Basic Green 1 (C.I. No. 42,040) were converted to a lake with a phosphomolybdic acid. Compared with the pigment of Comparative Example 2, the resulting pigment had the advantageous performance characteristics described in Example 1, when used in offset printing inks and nitrocellulose-containing printing inks.
• a heteropolyacid solution prepared in a conventional manner from 33.2 parts of molybdenum oxide, and 3.14 parts of disodium phosphate in 320 parts of water was added to a solution of 38 parts of Basic Violet 1 (C.I. No. 42,535) in 2800 parts of water, the pigment being precipitated.
• the phosphomolybdic acid solution according to Example 5 was added to an aqueous solution of 38 parts of C.I. Basic Violet 1 (C.I. No. 42,535) in 2800 parts of water, the pigment being precipitated. Thereafter, 2 parts of sodium ethylenediaminetetraacetate and 16 parts of emulsion were added, as described in Example 5. The suspension was stirred for one hour at 80° C., after which the pigment was isolated, and dried at 75° C. in a through-circulation oven.
• C.I. Basic Violet 1 C.I. No. 42,535
• Comparative Example 5 was repeated, except that the pigment suspension was stirred for one hour at 90° C. instead of 80° C.
• Example 5 The procedure described in Example 5 was followed, except that, instead of C.I. Basic Violet 1 (C.I. No. 42,535), 38 parts of C.I. Basic Violet 3 (C.I. No. 42,555) were used for the laking procedure. Compared with the pigment of Comparative Example 5, the pigment obtained had the advantageous performance characteristics stated in Example 1.
• Example 5 was repeated, except that, instead of the acidic phosphate, 13 parts of dodecylbenzenesulfonic acid were added to the crude pigment suspension. Furthermore, stirring was then carried out for one hour at 90° C. instead of 80° C. Compared with the pigment of Comparative Example 4, the pigment obtained had the advantageous performance characteristics stated in Example 1.
• Example 6 was repeated, except that 10 parts of a reaction product of nonylphenol with 10 moles of EO were used instead of the acidic phosphate. Moreover, stirring was then continued for one hour at 90° C. instead of 80° C. Compared with the pigment of Comparative Example 6, the pigment obtained had the advantageous performance characteristics stated in Example 1.
• Example 5 was repeated, except that 10 parts of a reaction product of isodecanol with 7 moles of EO were used instead of the acidic phosphate. Furthermore, stirring was then continued for one hour at 90° C. instead of 80° C. Compared with the pigment of Comparative Example 4, the pigment obtained had the advantageous performance characteristics stated in Example 1.
• Example 5 The procedure described in Example 5 was followed, except that 10 parts of a sodium salt of a sulfated C 12 -C 14 -alcohol/EO adduct were used instead of the acidic phosphate. Furthermore, the pigment suspension was then stirred for a further hour at 90° C. instead of 80° C. Compared with the pigment of Comparative Example 4, the pigment obtained had the advantageous performance characteristics stated in Example 1.
• Example 5 The procedure described in Example 5 was followed, except that 6.8 parts of dodecylbenzenesulfonic acid and 6.2 parts of N,N-dimethyloctadecylamine were used instead of the acidic phosphate. Furthermore, the pigment suspension was then stirred for a further hour at 90° C. instead of 80° C. Compared with the pigment of Comparative Example 4, the pigment obtained had the advantageous performance characteristics stated in Example 1.
• Example 5 was repeated, except that 13 parts of ⁇ -naphthol were used instead of the acidic phosphate. Compared with the pigment of Comparative Example 4, the pigment obtained had the advantageous performance characteristics stated in Example 1.
• a heteropolyacid prepared in a conventional manner from 4.96 parts of molybdenum oxide, 35.16 parts of tungsten oxide and waterglass consisting of 0.59 part of silica in 380 parts of water was added to an aqueous solution of 38.6 parts of C.I. Basic Blue 7 (C.I. No. 42,595) in 2700 parts of water, the pigment being precipitated.
• a heteropolyacid prepared in a conventional manner from 4.96 parts of molybdenum oxide, 35.16 parts of tungsten oxide and waterglass consisting of 0.59 part of silica in 380 parts of water was added to an aqueous solution of 38.6 parts of C.I. Basic Blue 7 (C.I. No. 42,595) in 2700 parts of water, the pigment being precipitated.
• the pigment suspension was stirred for a further 15 minutes, and 1.74 parts of sodium ethylenediaminetetraacetate and 8.3 parts of an emulsion prepared from 0.53 part of oleic acid ethanolamide, 1.13 parts of a normal C 13 -C 15 -paraffin and 6.64 parts of water at 60° C. were added.
• the mixture was stirred for one hour, after which the pigment was isolated, dried at 75° C. in a through-circulation oven and milled.
• a phosphomolybdic acid prepared in a conventional manner from 48.51 parts of molybdenum oxide and 4.34 parts of disodium phosphate in 945 parts of water was added to a mixture of 55.35 parts of C.I. Basic Red 1 (C.I. No. 45,160), and 1.0 part of C.I. Basic Violet 11 (C.I. No. 45,175) in 2000 parts of water, the pigment being precipitated.
• a mixture of 7.19 parts of triisobutyl phosphate, 2.29 parts of an adduct of 20 moles of EO which 1 mole of isononylphenol and 0.52 part of an adduct of 5 moles of EO with 1 mole of isodecanol was added to the pigment suspension.
• a phosphomolybdic acid prepared in a conventional manner from 48.51 parts of molybdenum oxide and 4.34 parts of disodium phosphate in 945 parts of water was added to a mixture of 55.35 parts of C.I. Basic Red 1 (C.I. No. 45,160) and 1.0 part of C.I. Basic Violet 11 (C.I. No. 45,175) in 2000 parts of water, the pigment being precipitated.
• the suspension was stirred for 15 minutes at 70° C., after which 8.3 parts of an emulsion prepared from 0.53 part of oleic acid ethanolamide, 1.13 parts of a normal C 13 -C 15 -paraffin and 6.64 parts of water at 60° C. were added. Stirring was continued for a further hour at 70° C., after which the pigment was isolated, dried at 75° C. in a through-circulation oven and milled.
• a phosphomolybdic acid solution prepared in a conventional manner from 27.0 parts of molybdenum oxide and 2.55 parts of disodium phosphate in 255 parts of water was added to an aqueous solution of 38.6 parts of C.I. Basic Blue 7 (C.I. No. 42,595) in 2700 parts of water, the pigment being precipitated.
• a phosphomolybdic acid solution prepared in a conventional manner from 27.0 parts of molybdenum oxide and 2.55 parts of disodium phosphate in 255 parts of water was added to a mixture of 9.6 parts of an acidic phosphate, which contained, as the ester group, a product obtained by reacting a C 13 -C 15 -oxoalcohol mixture with 6 moles of PO and then with 12 moles of EO per mole of alcohol, and 38.6 parts of C.I. Basic Blue 7 (C.I. No. 42,595) in 2700 parts of water, the pigment being precipitated.
• Stirring was carried out for one hour at 70° C., after which the pigment was isolated, and dried at 75° C. in a through-circulation oven. Milling gave a readily dispersible pigment which, compared with the pigment of Comparative Example 9, had the advantageous performance characteristics stated in Example 1.
• a heteropolyacid solution prepared in a conventional manner from 51.6 parts of molybdenum oxide and 4.88 parts of disodium phosphate in 497 parts of water was added to a mixture of 38 parts of Basic Violet 1 (C.I. No. 42,535) and 15 parts of N,N-dimethyloctadecylamine in 2800 parts of water, the pigment being precipitated.
• Stirring was carried out for one hour at 90° C., after which 2 parts of sodium ethylenediaminetetraacetate and 16 parts of an emulsion prepared from 1.02 parts of oleic acid ethanolamide, 2.18 parts of a normal C 13 -C 15 -paraffin and 12.8 parts of water at 60° C.
• the pigment suspension was stirred for one hour at 90° C., after which 2 parts of sodium ethylenediaminetetraacetate and 16 parts of an emulsion prepared from 1.02 parts of oleic acid ethanolamide, 2.18 parts of a normal C 13 -C 15 -paraffin and 12.8 parts of water at 60° C.
• Example 4 Compared with the pigment of Comparative Example 4, the pigment obtained had the advantageous performance characteristics stated in Example 1.
• Example 18 The procedure described in Example 18 was followed, except that 15 parts of a sodium salt of a sulfated C 12 -C 14 -alcohol/EO adduct were used instead of the dodecylbenzenesulfonic acid. Compared with the pigment of Comparative Example 4, the pigment obtained had the advantageous performance characteristics stated in Example 1.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Inorganic Chemistry (AREA)
• Inks, Pencil-Leads, Or Crayons (AREA)
• Pigments, Carbon Blacks, Or Wood Stains (AREA)
• Detergent Compositions (AREA)
• Cosmetics (AREA)
• Paints Or Removers (AREA)

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• 1984
  • 1984-09-27 DE DE19843435433 patent/DE3435433A1/de not_active Withdrawn
• 1985
  • 1985-09-21 DE DE8585111968T patent/DE3584752D1/de not_active Expired - Lifetime
  • 1985-09-21 EP EP85111968A patent/EP0176059B1/de not_active Expired - Lifetime
  • 1985-09-26 US US06/780,317 patent/US4664715A/en not_active Expired - Lifetime
  • 1985-09-27 JP JP60212754A patent/JPS6185478A/ja active Pending

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